I don’t really know where to start with this one… and I also don’t know how mean I should be, because I have plans to see him again, and I’ve found being mean about someone is hard to come back from if I decide to change my mind.

So let’s start with this… His match.com profile pic was him in a cowboy hat. I’m a sucker for cowboys. Especially blue-eyed cowboys with dark hair… who have jobs… and seem normal. “Seem” normal.

I saw him originally, read through his whole profile, and swooned. Really, really good-looking. Sounded like we would get along really well. He sent me the original message, and I promptly replied. No messing around when it comes to sexual cowboys with jobs. Our chatter was brief before we exchanged numbers and he asked if I’d be interested in meeting him, to which I obviously replied yes.

This was about a week ago? He had plans late last week to go on a rafting trip (which later got canceled due to the fact that he found himself having to work all weekend), so he asked if I wanted to meet for coffee on Monday (yesterday). I’ve come to learn that although I had never been on a first date for coffee, it’s pretty common, and normal. I don’t find any sort of date normal that doesn’t involve alcohol, but I decided to grow up and embrace the coffee date. The strange thing was that he wanted to meet at a really awkward time, in Del Mar, which is in between where we both live. He suggested 4pm, which I thought was really weird. I do have a pretty flexible work schedule, but he didn’t know that. How many people can meet in a random town at 4pm on a Monday?? I told him I couldn’t guarantee the time, as I had to see how late my meeting lasted which was about a half hour away.

THEN… he friend requested me on Facebook. Ummmm…. no? I texted him and said I had a policy about accepting FB friends before I even met someone. He said he, unfortunately had the opposite policy, and promised himself he wouldn’t meet anyone in person again without being Facebook friends first, because he has learned his lesson (??), and he understood if I didn’t feel comfortable with it, but we’d have to cancel our date. Wait… what?

I wasn’t ready to give up on the sexual cowboy yet, so I strategically accepted him, blocking him from most of my tagged photos and posts (including my blogs, obvi). He was starting to seem very business-like and by-the-book, which was off-putting. What was also off-putting is when he immediately DE-FRIENDED me on Saturday evening when he said something obnoxious about being “too old” to go out in PB (which is the town I live in), and I came back at him with a sarcastic response. Of course, I called him out on de-friending me, and he said since I didn’t “seem interested,” he deleted me, because he likes to “keep his Facebook clean.”

WHAT DUDE???

Carissa was here for this entire conversation and she was like, “You are NOT meeting him. I hate him.”

But I obviously didn’t listen to her.

We brushed off our texting disagreement, and he asked if I was still interested in meeting him Monday, and I said “No harm in coffee.”

So coffee it was.

As I’m nearing the Starbucks yesterday late afternoon, I texted V: “I’m about to go on a sober first date. I don’t think I’ve ever done this before.”

She asked, “Are you nervous??”

“Yeah!! I’ve never been on a coffee date. Fear of the unknown. Kinda like a new gym.”

“Ugh I hate a new gym.” …A social awkwardness we share.

So I pull up and he’s sitting outside with an iced tea or something (I’m late… good excuse though, I swear). He’s on the phone. I walk right up and mouth a silent hello. He gives me the one minute sign, and tells whoever is on the other end of the phone to hold on a second. Then he turns to me (still sitting… not even getting up to say hi), “Do you want to go in and get a drink? I’ll be off the phone in one minute… sorry.”

I’m like, “Yeah, sure…”

And I walk into Starbucks. At this point I’m already feeling awkward. I literally feel like I’m going on an interview. Not a date interview… a business interview. I wait in line by myself to get my coffee, thinking… this is not a date.

I go back out, and sit across from him. He is off the phone now, but still shows no interest in hugging hello (is it weird that my natural reaction would be to hug hello??) We immediately get to talking about work, because we are obviously still mid-workday. Cowboy launches into a full account of not only his job, but the specific deals that are in the works right now with specific investors, and how the contracts are being drawn up. I’m like wwwwwttttttffffffff.

In between one of his first lectures on private equity or some sh*t, he pauses, and says, “You look really pretty.” At which point I awkwardly giggled like a 12-year-old because it was out of the blue and I didn’t know how else to react. I’m 30, I should have my act together at this point, having been on 3200 first dates, but no, I apparently do not.

The conversation evolves, and not only do I know exactly which jobs HE has had in the past 10 years, but I am fully briefed on his dad’s fashion business, and the way Walmart buys clothing. My head is spinning. I was not an economics major and I wasn’t prepared for such an in-depth conversation about the economic status of the world. He’s easy to talk to but the conversation feels very business-like. Could I hold the conversation? Yeah. Did I WANT to hold this conversation the first time meeting someone? No.

He interjected just a tad of personal talk into his business rants, and I asked if these things were always swirling around in his brain and he said yes. I think I could recite all the names of the attorneys he has worked with on deals in the past 8 years, as well as their children’s’ hobbies and hair color. Holy CRAP…. I needed a nap.

So after a really non-stop, packed out conversation, he looks at his watch a little before 6, and says, “Should we get going?” and before I could even grab my purse he was out of his seat and halfway into the parking lot. I literally thought he was going to just walk straight to his car without saying goodbye. My head was spinning and I was really confused. I stopped and said,

“Well my car is this way.” And I just stood in the middle of the parking lot. Like DUDE, give me a hug or at least a handshake. He stopped, turned around and gave me sort of half hug, half pat and said it was nice meeting me.

I got in my car with my head spinning… confused if I was just on an interview to be a business partner or if it was actually, a date. He didn’t like my one business idea I proposed, because he said I had a really “east-coast mindset,” so I’m assuming he didn’t want to continue into business together.

I wasn’t expecting to hear from him again, because whatever it was he wanted to get out of that meeting, I don’t think he got it. But the most confusing thing was trying to figure out WHAT he wanted to come of that meeting. Mid-day, outside a Starbucks. I don’t think either one of us got to really know anything about the other’s actual personality… unless his personality IS work, and ONLY work… which I tend to doubt, and it didn’t match up with what he had to say about himself on his profile.

Maybe he just had a lot on his mind? Maybe he was socially awkward??

He texted me about 2 hours later: “Thx for meeting me”

Oh really?? Like you could get anymore business. You can’t even spell out the word “thanks?”

I wrote back, “No prob. Good meeting you”

Thinking this was the end, he then says, “Let me know if you would like to go out again”

Wait WHAT??? That is not you asking me out. What does that even mean? And you gave me no signs during our first interaction that you even would WANT to see me again. Which obviously means I DO want to go out again. But I’m not going to make it completely easy. So,

“Would that be implying you’d like to go out again?”

“Yes please”

I said I would, and he suggested a pool day Saturday (he apparently has a pool), or something for football Sunday. I told him I couldn’t commit yet for this weekend because it’s my sister’s birthday weekend so I wanted to see what she wanted to do first. He said to just keep him posted and I said ok.

Then…. Mr. Business ends the conversation. The final text of the night.

He typed, “xo”

I literally LOLed. I think he is bi-polar. I really don’t know what’s wrong with him. I told Carissa, “Maybe I’ll marry him for money.”